2,3-Dichloropyrazine → HCID 59351251, compound

HRID 2191979Notes

Reaction equation

HRID 2191979 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[O:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1(C)C=CC=CC=1>[Cl:8][C:7]1[C:2]([C:12]2([C:15]([O:17][CH3:18])=[O:16])[CH2:13][CH2:14][O:9][CH2:10][CH2:11]2)=[N:3][CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 785752,3-DichloropyrazineHCID 2733832Lithium HexamethyldisilazideHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

Product 1

HCID 59351251HCID 59351251, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2,3-dichloropyrazine (1.45 g, 9.73 mmol) and methyl tetrahydro-2H-pyran-4-carboxylate (2.60 mL, 19.47 mmol) in Toluene (19.47 mL) at room temperature was added LiHMDS (19.47 mL, 19.47 mmol, 1M solution) dropwise. After overnight room temperature stirring, reaction was quenched with saturated NH4Cl solution and extracted with EtOAc. Purification by Biotage (0-10% MeOH/DCM) produced product.

Workup

  1. customreaction
  2. customwas quenched with saturated NH4Cl solution
  3. extractionextracted with EtOAc
  4. customPurification by Biotage (0-10% MeOH/DCM)
  5. customproduced product

Sources & evidence

ORD record
ord-53f2c76927694b22ac4a4f4e63b26980
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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